Apartments in Chestertown for Rent

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Mar 13 - Mar 15
In two months
Apr 24 - Apr 26
In three months
May 22 - May 24
In four months
Jun 19 - Jun 21

Our top choices for Chestertown apartments

Property grounds

Apartment in Chestertown

First Floor Studio Apartment in Historic Chestertown
9.6 out of 10, Exceptional, (108 reviews)
"Everything was clean and neat and welcoming "
United States
Iriana J.
$144 nightly
The price is $159
Mar 2 - Mar 3
Total with taxes and fees
First Floor Studio Apartment in Historic Chestertown
Fridge, microwave, oven, stovetop

Apartment in Historic District

18th Cent. Charm in Historic Downtown Annapolis
9.0 out of 10, Wonderful, (13 reviews)
"Great experience"
United States
David P.
$304 nightly
The price is $347
Feb 28 - Mar 1
Total with taxes and fees
18th Cent. Charm in Historic Downtown Annapolis
Living area

Apartment in Havre de Grace

Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace
10.0 out of 10, Exceptional, (5 reviews)
"It is a warm and welcoming little home away from home. We will be back!"
United States
Brittany C.
$180 nightly
The price is $191
Mar 1 - Mar 2
Total with taxes and fees
Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace
Beach

Apartment in Worton

Waterfront Retreat with Private Dock and Beach
10.0 out of 10, Exceptional, (25 reviews)
"The apartment, including kitchen and bathroom, was very clean. Plenty of linens available for use. Perfect spot for fishing off of their dock. Very pleased with our reservation. "
United States
Debbie S.
$284 nightly
The price is $314
Mar 1 - Mar 2
Total with taxes and fees
Waterfront Retreat with Private Dock and Beach
Exterior

Apartment in Millington

Guest Suite for up to 2 in a Victorian on the Chester River
9.6 out of 10, Exceptional, (20 reviews)
"So pleased with all aspects of my stay. Clean, Comfortable, Quiet, Amenities all beyond expectation."
United States
Cynthia C.
$118 nightly
The price is $125
Mar 24 - Mar 25
Total with taxes and fees
Guest Suite for up to 2 in a Victorian on the Chester River
Beach

Apartment in Rock Hall

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
10.0 out of 10, Exceptional, (17 reviews)
"Close to Main Street. Very nice and spacious accommodations."
United States
Michael D.
$259 nightly
The price is $286
Feb 28 - Mar 1
Total with taxes and fees
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Marina

Apartment in Fells Point

Cozy Fells Point Gem / In The Heart of Fells Point
9.8 out of 10, Exceptional, (202 reviews)
"Amazing all around! Owner didn't miss a beat with communication, great location, cozy and quiet stay "
United States
Leanne
$177 nightly
The price is $204
Mar 18 - Mar 19
Total with taxes and fees
Cozy Fells Point Gem / In The Heart of Fells Point
Outdoor pool, a heated pool

Apartment in Annapolis

Waterfront Oasis of Annapolis Star
10.0 out of 10, Exceptional, (81 reviews)
"Owners were great hosts. Loved this property!"
United States
Thomas
$363 nightly
The price is $414
Feb 28 - Mar 1
Total with taxes and fees
Waterfront Oasis of Annapolis Star
Fridge, microwave, oven, stovetop

Apartment in Cape Saint Claire

Luxury Pool Loft sleeps 4
10.0 out of 10, Exceptional, (4 reviews)
"This place has a fantastic location and an incredibly welcoming host! The area also features wonderful walking trails."
United States
Ana S.
$343 nightly
The price is $391
Mar 1 - Mar 2
Total with taxes and fees
Luxury Pool Loft sleeps 4
Interior

Apartment in Greektown

Cozy 2-bedroom apartment in welcoming Baltimore with WiFi, AC
9.6 out of 10, Exceptional, (9 reviews)
"The house was clean and the beds were comfortable. "
United States
Karen B.
$196 nightly
The price is $226
Mar 2 - Mar 3
Total with taxes and fees
Cozy 2-bedroom apartment in welcoming Baltimore with WiFi, AC
Terrace/patio

Apartment in Kent County

High Tide Haven Suite
$196 nightly
The price is $203
Feb 28 - Mar 1
Total with taxes and fees
High Tide Haven Suite
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties

The Annual Vacation Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
Book now
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chestertown Hotel Reviews

Courtyard by Marriott Baltimore Downtown/McHenry Row

Courtyard by Marriott Baltimore Downtown/McHenry Row

10/10 Excellent
"Very nice hotel would return"
Shari 1-night trip
Posted 3 days ago
Courtyard by Marriott Baltimore Downtown/McHenry Row

Find out more about Chestertown

Chestertown Apartments information

Number of reviews
467
Accommodation
80 Apartments
Lowest Price
$125
Highest Price
$414

Frequently asked questions

What's it like to stay at an apartment in Chestertown?
You can choose from 6 apartments in Chestertown for your vacation.
Why should you consider apartments instead of traditional hotels?
An apartment comes equipped with a kitchen, so you can cook some of your meals, and usually is more spacious than a traditional hotel room. Apartments are a good option for solo travelers who want to live like locals, and also for families wanting the conveniences of home.
What's the top apartment for my stay in Chestertown?
First Floor Studio Apartment in Historic Chestertown: Includes a private pool, laundry facilities, and free WiFi. A fitness center and onsite laundry facilities are on site. Historic 2 Bed/2 Bath Downtown Loft w/Park View & Spa Access: Free WiFi, private balconies, and Smart TVs are included. Access to onsite laundry facilities is available on site.
How many apartments can I expect to find in Chestertown?
Expedia has 6 apartments to book in Chestertown.
What can I expect from the weather during my trip to Chestertown?
Weather is only one factor, but it can really affect your travel plans, especially when you're planning an extended stay in Chestertown. The hottest months are usually July and August with an average temp of 74°F, while the coldest months are January and February with an average of 39°F. Average annual precipitation for Chestertown is 48 inches.
What should I see and do in Chestertown?
Cultural attractions include Historical Society of Kent County Maryland and Garfield Center for the Arts at the Prince Theater, whereas Northern Chesapeake Bay and Chesapeake Bay are a couple of picturesque spots to enjoy the outdoors. Other places in town to visit include Chestertown Historic District and Rolphs Wharf Marina.
What's the best way to get to and around Chestertown?
Knowing a bit about the transportation options can make your trip smoother when you get to your destination. Fly into Baltimore, MD (MTN-Martin State), which is located 20.3 mi (32.7 km) from the heart of the city. Otherwise, you can search for flights to Easton, MD (ESN-Easton - Newnam), which is 28.2 mi (45.3 km) away. If you'd like to explore around the area, consider renting a car to take in more sights.

Explore a world of travel with Expedia